The mission, tough as it might sound to an urban sophisticate such as myself, should not have been impossible. In a bid to prove that it is possible for a young man to dress with style and finesse wherever he lives in the UK (even Wales), I was to spend a day in the middle of nowhere, scouring local shops for wearable, affordable and, yes, even fashionable clothing that I would willingly bring back to London and absorb into my everyday wardrobe.

Advertisement - Continue Reading Below

I had less than 24 hours and no fixed abode, so the internet was clearly out: no time to hang around waiting for smartly wrapped parcels to be delivered. High street chains and department stores, even if I could find any in the back of beyond, would be regarded as cheating, by my editor at least. Independents and charity shops, on the other hand, were encouraged. I had been given £200 to spend on an outfit, which, for a spoilt London style director, didn't feel like much to work with. But that wasn't the cause of my trepidation. The thing is, if you grew up anywhere other than London — OK, or Manchester or Leeds or Newcastle (and even then…) — you'll know that you don't typically stumble across interesting, fashionable men's clothes while you wander the streets of our island.

I was raised in a village called Fetcham in Surrey, only 20 miles from central London, but the proverbial world away, certainly in the style stakes. My exposure to men's fashion was limited to the stuff I saw on the pages of magazines. The clothes presented on the pages of Esquire, sorry to say, were not available for purchase in Fetcham, or even in Guildford, our nearest big town. So, when it was suggested I return to the sartorial wilderness on a retail expedition to prove my teenage self wrong — yes, you can actually dress well without regular visits to W1 — I must admit I was sceptical.

The original idea came from our cousins across the pond: last year, American Esquire's fashion director, Nick Sullivan, was sent to the geographical centre of the US (Lebanon, Kansas, it turns out), stripped down to nothing but his boxer shorts and a vest, and challenged to find clothes he would actually want to wear, on a budget of $200. The clothes Nick found in Kansas reflected the character of that unpretentious, rural Midwestern state: solid work boots, which he snapped up for a song, and some pretty natty vintage military jackets.

Advertisement - Continue Reading Below

What is the UK equivalent of Kansas? After some debate in the office, I decided I would start my style odyssey in Britain's smallest city, St Davids in Wales. A tiny settlement perched on the furthest westerly mainland point of the rugged county of Pembrokeshire, it seemed an agreeably remote place in which to begin.

After an eight-hour drive along the M4 from London, I started my search in St Davids' tiny City Hall, a honey-hued building, which, alongside a newsagent, plays host to a miniature charity shop run by a pair of charming ladies, Grace Davies and Mary Trott. They told me that they'd recently dressed a 16-year-old local boy for a "do" for 50 pence. In that spirit, I snapped up a chunky teal fishmerman's jumper for the bargain price of four pounds.

Motivated by my positive start and the knowledge you can get dressed for a night out in this part of the world for half a pound, I headed further into town, stopping local men for shopping tips along the way.

"I never buy clothes from St Davids, ever. If I'm going away, or if I'm going to Cardiff, I go shopping there. If I need anything proper, I go to the bigger shops in Haverfordwest," Oliver Blakiston, the young manager of St Davids' Cross Hotel, told me. It was a sentiment echoed by 23-year-old gallery worker Sean Judge. "I live in Haverfordwest," he said, "but I do all my clothes shopping online. That said, I went to Bristol last week and did some shopping there. If you're into fashion, you're not going to shop in Pembrokeshire. It's really limited. There's nothing — no Topman, no H&M, no JD. Nothing at all."

Advertisement - Continue Reading Below

Advertisement - Continue Reading Below

Undeterred by these less than glowing reports on the region's shopping, and following a quick look around the monolithic medieval cathedral, which boasts some of the UK's most extraordinary wood carvings this side of William the Conqueror, I set a course for Haverfordwest, 10 miles inland from the city and the most populous settlement in Pembrokeshire, boasting 14,596 residents at last count. I struggled to believe that I wouldn't find something good in a town with a name that translates into "ford used by fat cows".

The first thing that struck me about Haverfordwest was the extraordinary number of empty shop fronts. I counted seven "closed down" signs on the shopping street leading down into the town centre. My first stop was a gentlemen's outfitters, careworn as a favourite old cardigan, called Matthew Locke. It seemed to be doing a relatively brisk trade.

"Business is very good," Matthew Locke himself told me. "Our customers come in and support us because they get what they like and they get good service. We look after our customers."

These customers, Locke continued, are not interested in fashion. They require only clothes that "work hard and do the job". He was sporting a generously proportioned brown suit and a beige shirt. The garments in his shop, he explained, are organised by type. Brightly coloured jumbo cords in equally jumbo cuts are lined up crotch-to-crotch against one wall. Equally roomy tweed jackets are scrunched on a rail together on another wall. Matthew Locke also offers a wide array of jazzy argyle jumpers.

When Locke finished serving a loyal octogenarian customer, I asked him where the young men of Haverfordwest go for their clothes. "Further afield," he said. "Youngsters want high-fashion brands but there's not a big enough market to demand it and we'd have to change our model entirely. We don't want to shoot the goose that lays the golden egg." That said, however: "Lots of our newer customers are looking for trendier stuff, so we have to move on a bit. People want slimmer-cut shirts, perhaps slimmer-cut suits. People also want fashion colours." Such as? "Blue is very popular."

Advertisement - Continue Reading Below

Digging deeper into Locke's stock I found a number of items, which, with a tweak, I would definitely wear. There was a smart Harris Tweed blazer from a brand called Torre, which, with the assistance of a tailor, would fit perfectly, and work when worn with more contemporary items such as slim-cut indigo jeans and fine-gauge cashmere roll-necks. Locke also offers a wide array of beautiful boots and shoes by Barker and Joseph Cheaney, among others. With prices starting around £200 a pair they were beyond my budget, but still prove that Haverfordwest is by no means a dead loss in the style stakes.

Bolstered, I headed to the only other men's shop in town, a tiny, independent sportswear store called The Pines. Though I found nothing to buy among the rails of skater T-shirts and board shorts — it was December in Wales and I'm 28 years old — store owner Kayleigh Rogers shed some light on the way local men dress.

"It's funny, when you go out you can tell who the younger lads are, because they're the ones who get suited and booted. They want to dress like the Essex boys they see on TV," she laughs. "But as guys get older they slowly morph back into the Pembrokeshire way and just wear scabby jeans and T-shirts out. My friend Adam is the only person I know who is into designer clothes, but he can only get that stuff in London. He even went up to Edinburgh to buy a coat last week. That's how far you need to go for good stuff."

Advertisement - Continue Reading Below

Advertisement - Continue Reading Below

Feeling slightly desperate, I decided to drive back out of town to visit the Solva Woollen Mill, which I'd spied on the road to St Davids. Set on the edge of a tiny stream and enveloped by overgrown pine trees, the mill looked like the kind of place where your grandma would have bought clothes back in the day, with walls made of wood, and woollen jumpers, scarves and blankets piled up to the (dangerously low) ceiling.

Here, I managed to find a roughly knitted wool tie in taupe, which wouldn't have looked out of place on the shelves of Drake's in Mayfair (it was a snip at £14). Meanwhile, Esquire photographer Chris Floyd bought an immaculately knitted fisherman's jumper (£40). With a more positive head on my wool-clad neck, I headed back to Haverfordwest on a lead that there was an army surplus store somewhere in town that I'd missed first time around.

Garishly lit and organised like a jumble sale, Brewer Army Surplus on Bridge Street in Haverfordwest has the boiled mushroom scent of a place that only sells second-hand clothing. Greeted by two weather-beaten Welsh ladies, eager to dress me, and a sea of muddy greens, easy greys and imperial blues, I felt what was left of the £200 start to burn a hole in my pocket.

A cropped navy blue RAF bomber jacket cut from thick cotton had a soft feel and a smart, clipped cut — not dissimilar to the jackets Prada showed for autumn/winter 2015, in fact. It fitted like a dream and was a bargain at £18. Sticking with the RAF theme, a ribbed, midnight blue jumper with epaulettes and elbow patches looked great beneath the simplicity of my new bomber. High quality and functional (fighter pilots don't want jumpers that won't keep them warm), the pullover was a steal at £20, and of higher quality than most sweaters you'll find on the High Street.

Advertisement - Continue Reading Below

My energy levels replete (the lunchtime scampi and chips was working its magic), the bargains continued to jump from the rails. The olive-green, sleeveless, quilted liner of an oversized TA parka looked great worn beneath my bomber and was only £8. A pair of calf-skimming dusty suede US Army desert combat boots would have looked great with some jeans but were a little small for me, so had to be left behind.

Speaking of denim, it wasn't just military gear on sale in Brewers — a pair of bleached denim Lee jeans, similar to those worn by Marty McFly in Back to the Future, was probably my star buy. The high-waisted, Eighties style with a straight-cropped leg felt surprisingly modern and clean cut, and looked great with the Converse high-tops I'd picked up for a fiver in one of the charity shops in town. What's more, they cost a mere £14, less than you'd pay for lunch from Whole Foods in London.

My final purchase, the most expensive at a whopping £30, was an updated version of my M65 army jacket. Perfect for my ape-like arms, the nip in the waist and density of fabric made me think of something I tried on in Saint Laurent a few years ago (though that jacket came in at around £800), and the subtle camouflage pattern looked surprisingly elegant when worn with my usual uniform of blue wool trousers, white T-shirt and charcoal wool overshirt.

What was most surprising about this unexpected treasure trove of reasonably priced army surplus gear was how every garment reminded me of the clothing I'd recently seen on the runways of London, Paris and Milan. It's long been said that men are drawn to clothes that boast function over form, and nowhere is this more prevalent than in military garb.

The boot of my Range Rover Evoque now full, I headed back to my hotel in St Davids to try my new outfits on for size. Having only spent £113 of my £200 budget, I couldn't help but feel smug with my haul. The clothes I found were wearable, smart and serviceable. OK, I didn't find much in the way of affordable tailoring — short of a few four-button plastic suits from charity shops — but if nothing else, my 24-hour odyssey in Wales proved that with a bit of imagination (and a slightly panicked few hours of searching) it's more than possible to dress well, even if you live in the back end of beyond.